RU2808989C1 - Use of methyl 2-(2-amino-2-oxo-1-cyanoethyl)-4-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-5-oxo-1-phenyl 2-(4-chlorophenyl)-2,5-dihydro-1h-pyrrole-3-carboxylate as an antioxidant agent - Google Patents
Use of methyl 2-(2-amino-2-oxo-1-cyanoethyl)-4-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-5-oxo-1-phenyl 2-(4-chlorophenyl)-2,5-dihydro-1h-pyrrole-3-carboxylate as an antioxidant agent Download PDFInfo
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- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims 2
- 230000003078 antioxidant effect Effects 0.000 abstract description 13
- -1 methyl 2-(2-amino-2-oxo-1-cyanoethyl)-4-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-yl)-5-oxo-1-phenyl-2-(4-chlorophenyl)-2,5-dihydro-1H-pyrrole-3-carboxylate Chemical compound 0.000 abstract description 12
- 239000003814 drug Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- WCBPJVKVIMMEQC-UHFFFAOYSA-N 1,1-diphenyl-2-(2,4,6-trinitrophenyl)hydrazine Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NN(C=1C=CC=CC=1)C1=CC=CC=C1 WCBPJVKVIMMEQC-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 4
- WIFCKLPZYYALGY-UHFFFAOYSA-N 1h-pyrrole-2,3-dione Chemical compound O=C1NC=CC1=O WIFCKLPZYYALGY-UHFFFAOYSA-N 0.000 description 3
- RTNPPPQVXREFKX-UHFFFAOYSA-N 4-hydroxy-1-methylquinolin-2-one Chemical compound C1=CC=C2C(O)=CC(=O)N(C)C2=C1 RTNPPPQVXREFKX-UHFFFAOYSA-N 0.000 description 3
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-1H-quinolin-2-one Natural products C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003219 pyrazolines Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- IBDRVPYRDAJOIC-UHFFFAOYSA-N C1NNC=C1.O=c1ccc2ccccc2[nH]1 Chemical compound C1NNC=C1.O=c1ccc2ccccc2[nH]1 IBDRVPYRDAJOIC-UHFFFAOYSA-N 0.000 description 1
- 102000003820 Lipoxygenases Human genes 0.000 description 1
- 108090000128 Lipoxygenases Proteins 0.000 description 1
- BERPCVULMUPOER-UHFFFAOYSA-N Quinolinediol Chemical class C1=CC=C2NC(=O)C(O)=CC2=C1 BERPCVULMUPOER-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000007760 free radical scavenging Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- BUTPBERGMJVRBM-UHFFFAOYSA-N methanol;methylsulfinylmethane Chemical compound OC.CS(C)=O BUTPBERGMJVRBM-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000010490 three component reaction Methods 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
Abstract
Description
Изобретение относится к области фармакологии и медицины, а именно к применению индивидуального соединения - метил 2-(2-амино-2-оксо-1-цианоэтил)-4-(4-гидрокси-1-метил-2-оксо-1,2-дигидрохинолин-3-ил)-5-оксо-1-фенил-2-(4-хлорфенил)-2,5-дигидро-1H-пиррол-3-карбоксилата, обладающего антиоксидантной активностью, который может найти применение в фармакологии и медицине в качестве антиоксидантного средства.The invention relates to the field of pharmacology and medicine, namely to the use of an individual compound - methyl 2-(2-amino-2-oxo-1-cyanoethyl)-4-(4-hydroxy-1-methyl-2-oxo-1,2 -dihydroquinolin-3-yl)-5-oxo-1-phenyl-2-(4-chlorophenyl)-2,5-dihydro-1H-pyrrole-3-carboxylate, which has antioxidant activity, which can be used in pharmacology and medicine as an antioxidant agent.
Заявленное соединение метил 2-(2-амино-2-оксо-1-цианоэтил)-4-(4-гидрокси-1-метил-2-оксо-1,2-дигидрохинолин-3-ил)-5-оксо-1-фенил-2-(4-хлорфенил)-2,5-дигидро-1H-пиррол-3-карбоксилат (1) и способ его синтеза известны из уровня техники. Соединение (1) получается в результате трехкомпонентной реакции пирролдиона (2), малононитрила и 4-гидрокси-1-метилхинолин-2(1Н)-она (3) под действием основания триэтиламина (Et3N) - (Salnikova Т. V., Sabitov A. A., Dmitriev М. V., Maslivets A. N., Rubin М. Substrate-dependent regiodivergent three-component condensation of 1H-pyrrole-2,3-diones, malononitrile and 4-hydroxyquinolin-2(1H)-ones // Tetrahedron. - 2021. - Vol.88. - P. 132129. DOI: 10.1016/j.tet.2021.132129), согласно схеме, представленной ниже:The claimed compound is methyl 2-(2-amino-2-oxo-1-cyanoethyl)-4-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-5-oxo-1 -phenyl-2-(4-chlorophenyl)-2,5-dihydro-1H-pyrrole-3-carboxylate (1) and the method for its synthesis are known from the prior art. Compound (1) is obtained as a result of a three-component reaction of pyrroledione (2), malononitrile and 4-hydroxy-1-methylquinolin-2(1H)-one (3) under the action of triethylamine base (Et 3 N) - (Salnikova T. V., Sabitov A.A., Dmitriev M.V., Maslivets AN, Rubin M. Substrate-dependent regiodivergent three-component condensation of 1H-pyrrole-2,3-diones, malononitrile and 4-hydroxyquinolin-2(1H)-ones // Tetrahedron. - 2021. - Vol.88. - P. 132129. DOI: 10.1016/j.tet.2021.132129), according to the diagram presented below:
Антиоксидантные свойства соединения (1) или его близких аналогов не изучены. Из уровня техники можно выделить гибридные производные гидроксихинолинонов и пиразолинов (4) (Kostopoulou I., Diassakou А., Kavetsou Е., Kritsi Е., Zoumpoulakis P., Pontiki E., Hadjipavlou-Litina D., Detsi A. Novel quinolinone-pyrazoline hybrids: Synthesis and evaluation of antioxidant and lipoxygenase inhibitory activity // Molecular Diversity. - 2021. - Vol.25. - PP. 723-740. DOI: 10.1007/s11030-020-10045-x), обладающие антиоксидантной активностью.The antioxidant properties of compound (1) or its close analogues have not been studied. From the prior art, hybrid derivatives of hydroxyquinolinones and pyrazolines (4) can be distinguished (Kostopoulou I., Diassakou A., Kavetsou E., Kritsi E., Zoumpoulakis P., Pontiki E., Hadjipavlou-Litina D., Detsi A. Novel quinolinone- pyrazoline hybrids: Synthesis and evaluation of antioxidant and lipoxygenase inhibitory activity // Molecular Diversity. - 2021. - Vol. 25. - PP. 723-740. DOI: 10.1007/s11030-020-10045-x), which have antioxidant activity.
Целью изобретения является изыскание новых соединений, обладающих антиоксидантной активностью, что позволит расширить ассортимент потенциальных антиоксидантных средств.The purpose of the invention is to find new compounds with antioxidant activity, which will expand the range of potential antioxidant agents.
Поставленная цель решается изучением антиоксидантной активности метил 2-(2-амино-2-оксо-1-цианоэтил)-4-(4-гидрокси-1-метил-2-оксо-1,2-дигидрохинолин-3-ил)-5-оксо-1-фенил-2-(4-хлорфенил)-2,5-дигидро-1H-пиррол-3-карбоксилата (1), который обладает антиоксидантной активностью - связывание свободных радикалов дифенилпикрилгидразина (DPPH) 68.4%. Изобретение иллюстрируется следующими примерами.This goal is achieved by studying the antioxidant activity of methyl 2-(2-amino-2-oxo-1-cyanoethyl)-4-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-5 -oxo-1-phenyl-2-(4-chlorophenyl)-2,5-dihydro-1H-pyrrole-3-carboxylate (1), which has antioxidant activity - free radical scavenging of diphenylpicrylhydrazine (DPPH) 68.4%. The invention is illustrated by the following examples.
Пример 1. Получение метил 2-(2-амино-2-оксо-1-цианоэтил)-4-(4-гидрокси-1-метил-2-оксо-1,2-дигидрохинолин-3-ил)-5-оксо-1-фенил-2-(4-хлорфенил)-2,5-дигидро-1H-пиррол-3-карбоксилата (1).Example 1. Preparation of methyl 2-(2-amino-2-oxo-1-cyanoethyl)-4-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-5-oxo -1-phenyl-2-(4-chlorophenyl)-2,5-dihydro-1H-pyrrole-3-carboxylate (1).
К раствору 1 ммоль пирролдиона (2), 1 ммоль малононитрила и 1 ммоль 4-гидрокси-1-метилхинолин-2(1H)-она (3) в 10 мл безводного тетрагидрофурана при перемешивании добавляли 0.2 ммоль триэтиламина. Реакционную смесь кипятили в течение 3 часов, охлаждали до комнатной температуры, растворитель упаривали при пониженном давлении. Остаток перекристаллизовывали из смеси толуол-этилацетат (1:1). Выход 47%, т.пл. 212-214°С (разд.). Соединение (1) C31H23ClN4O6. Устойчиво при хранении в обычных условиях.To a solution of 1 mmol of pyrroledione (2), 1 mmol of malononitrile, and 1 mmol of 4-hydroxy-1-methylquinolin-2(1H)-one (3) in 10 ml of anhydrous tetrahydrofuran, 0.2 mmol of triethylamine was added with stirring. The reaction mixture was boiled for 3 hours, cooled to room temperature, and the solvent was evaporated under reduced pressure. The residue was recrystallized from a toluene-ethyl acetate mixture (1:1). Yield 47%, mp. 212-214°C (section). Compound (1) C 31 H 23 ClN 4 O 6 . Stable when stored under normal conditions.
ИК спектр (в вазелиновом масле), см-1: 3482, 3288, 3240, 31.56, 3105, 2242, 1716, 1705, 1689, 1668, 1652, 1617.IR spectrum (in Vaseline oil), cm -1 : 3482, 3288, 3240, 31.56, 3105, 2242, 1716, 1705, 1689, 1668, 1652, 1617.
Соотношение диастереомеров dr 11.5: 1 (А : В) по данным ЯМР 1H. Спектр 1Н ЯМР (400 МГц, DMSO-db) δ, м.д. (для обоих диастереомеров: А+В): [10.81 (с, А), 9.71 (с, В), Σ1H], 8.24 (уш. с, 0.08Н, В), [8.1.0 (дд, J=8.1, 1.5 Гц, А), 8.06 (дд, J=8.0, 1.5 Гц, В), Σ1H], 7.81. - 7.55 (м, 7.76Н), 7.45 (д, J=8.7 Гц, 0.16Н, В), 7.38 - 7.29 (м, 4Н), [6.98 - 6.92 (м, А), 6.68 - 6.64 (м, В), Σ2H], [5.44 (с, А), 5.14 (с, В), Σ1H], [3.64 (с, В), 3.62 (с, А), Σ3H], [3.47 (с, В), 3.41 (с, А), Σ3Н].The ratio of diastereomers is dr 11.5: 1 (A : B) according to 1 H NMR data. 1 H NMR spectrum (400 MHz, DMSO-d b ) δ, ppm. (for both diastereomers: A+B): [10.81 (s, A), 9.71 (s, B), Σ1H], 8.24 (br.s, 0.08H, B), [8.1.0 (dd, J=8.1 , 1.5 Hz, A), 8.06 (dd, J=8.0, 1.5 Hz, V), Σ1H], 7.81. - 7.55 (m, 7.76Н), 7.45 (d, J=8.7 Hz, 0.16Н, V), 7.38 - 7.29 (m, 4Н), [6.98 - 6.92 (m, A), 6.68 - 6.64 (m, V ), Σ2H], [5.44 (s, A), 5.14 (s, B), Σ1H], [3.64 (s, V), 3.62 (s, A), Σ3H], [3.47 (s, V), 3.41 (c, A), Σ3Н].
Спектр 13С ЯМР (101 МГц, DMSO-d6) δ, м.д. (для основного диастереомера А): 167.7, 162.9, 162.0, 160.4, 158.6, 145.4, 139.4, 138.2,134.7, 134.2,133.6, 131.9, 129.1 (2С), 128.6 (2С), 128.5 (2С), 128.5 (2С), 128.1,123.6, 121.6, 115.5, 114.9, 114.7, 103.0, 71.4, 51.7, 40.1, 29.2. 13 C NMR spectrum (101 MHz, DMSO-d 6 ) δ, ppm. (for the main diastereomer A): 167.7, 162.9, 162.0, 160.4, 158.6, 145.4, 139.4, 138.2,134.7, 134.2,133.6, 131.9, 129.1 (2C), 128.6 (2C), 128.5 (2C ), 128.5 (2C) , 128.1,123.6, 121.6, 115.5, 114.9, 114.7, 103.0, 71.4, 51.7, 40.1, 29.2.
HRMS (EST+): m/z [М+Н]+ вычислено для C31H23ClN4O6: 583.1379; найдено: 583,1380HRMS (EST+): m/z [M+H] + calculated for C 31 H 23 ClN 4 O 6 : 583.1379; found: 583.1380
Пример 2. Исследование антиоксидантной активности соединения (1).Example 2. Study of the antioxidant activity of compound (1).
Антиоксидантная активность изучалась спектрофотометрическим методом по способности растворов исследуемых веществ улавливать ярко окрашенные радикалы 2,2~дифенил-1-пикрилгидразила (DPPH) [Moore J. С, Liangli L. Yu. P. 118-172. DOI: 10.1002/9780470228333. CH9; Wheat Antioxidants (ed. Liangli Yu). Wiley. 2008. DOT: 1.0.1002/9780470228333].Antioxidant activity was studied by the spectrophotometric method by the ability of solutions of the studied substances to capture brightly colored 2,2~diphenyl-1-picrylhydrazyl (DPPH) radicals [Moore J. C, Liangli L. Yu. P. 118-172. DOI: 10.1002/9780470228333. CH9; Wheat Antioxidants (ed. Liangli Yu). Wiley. 2008. DOT: 1.0.1002/9780470228333].
Фотометрический DPPH реагент содержал 0.2 мМ раствор DPPH в метаноле. Растворы (концентрация 15 мкмоль/мл) исследуемых соединений и эталонов (агидол-1, аскорбиновая кислота) в ДМСО в количестве 100 мкл добавлялись к DPPH реагенту (100 мкл) в лунки 96-луночного планшета. Реакционная смесь выдерживалась при 20°С в течение 20 мин в темноте. Оптическую плотность реакционных смесей измеряли при длине волны 517 им. Калибровка проводилась по свежеприготовленному раствору DPPH в смеси ДМСО-метанол, 1 к 1. Убыль радикала, рассчитывали по формуле:The photometric DPPH reagent contained a 0.2 mM solution of DPPH in methanol. Solutions (concentration 15 µmol/ml) of the studied compounds and standards (agidol-1, ascorbic acid) in DMSO in an amount of 100 µl were added to the DPPH reagent (100 µl) into the wells of a 96-well plate. The reaction mixture was kept at 20°C for 20 min in the dark. The optical density of the reaction mixtures was measured at a wavelength of 517 nm. Calibration was carried out using a freshly prepared DPPH solution in a DMSO-methanol mixture, 1 to 1. The loss of the radical was calculated using the formula:
Убыль радикала (%) = [(А0 - A1)/A0]⋅100, где А0 - поглощение раствора DPPH без исследуемого образца, А] - поглощение раствора DPPH вRadical loss (%) = [(A 0 - A 1 )/A 0 ]⋅100, where A 0 is the absorption of the DPPH solution without the test sample, A] is the absorption of the DPPH solution in
присутствии исследуемого образца.presence of the test sample.
Результаты исследований приведены в Таблице.The research results are shown in the Table.
Проведенные исследования показали (см. таблицу), что соединение (1) проявляет выраженную антиоксидантную активность в отношении свободного радикала DPPH, сопоставимую с активностью эталонов.Studies have shown (see table) that compound (1) exhibits pronounced antioxidant activity against the free radical DPPH, comparable to the activity of the standards.
Предлагаемое соединение метил 2-(2-амино-2-оксо-1-цианоэтил)-4-(4-гидрокси-1-метил-2-оксо-1,2-дигидрохинолин-3-ил)-5-оксо-1-фенил-2-(4-хлорфенил)-2,5-дигидро-1H-пиррол-3-карбоксилат (1) обладает антиоксидантной активностью и может найти применение в фармакологии в качестве потенциального антиоксидантного лекарственного средства.The proposed compound is methyl 2-(2-amino-2-oxo-1-cyanoethyl)-4-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-5-oxo-1 -phenyl-2-(4-chlorophenyl)-2,5-dihydro-1H-pyrrole-3-carboxylate (1) has antioxidant activity and can be used in pharmacology as a potential antioxidant drug.
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| RU2764906C1 (en) * | 2021-07-05 | 2022-01-24 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" (ПГНИУ) | METHOD FOR THE PREPARATION OF 3-ARYL-N-BENZYL-2-HYDROXY-1-OXOBENZO[d]PYRROLO[2,1-b]THIAZOLE-3a(1H)-CARBOXAMIDES |
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